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  • 695459 - 1,3,5,7-Tetramethyl-6-phenyl-2,4,8-trioxa-6-phosphaadamantane

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695459 Sigma-Aldrich

1,3,5,7-Tetramethyl-6-phenyl-2,4,8-trioxa-6-phosphaadamantane

97%

Synonym: 1,3,5,7-Tetramethyl-8-phenyl-2,4,6-trioxa-8-phosphatricyclo[3.3.1.13,7]decane, meCgPPh

  • CAS Number 97739-46-3

  • Empirical Formula (Hill Notation) C16H21O3P

  • Molecular Weight 292.31

  •  PubChem Substance ID 329761744

  •  NACRES NA.22

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Properties

Related Categories Buchwald Ligands and Complexes, Buchwald and Related Ligands, Catalysis and Inorganic Chemistry, Chemical Synthesis, Cross-Coupling,
Quality Level   100
assay   97%
reaction suitability   reaction type: Buchwald-Hartwig Cross Coupling Reaction
  reaction type: Heck Reaction
  reaction type: Hiyama Coupling
  reaction type: Negishi Coupling
  reaction type: Sonogashira Coupling
  reaction type: Stille Coupling
  reaction type: Suzuki-Miyaura Coupling
  reagent type: ligand
reaction type: Cross Couplings
mp   106-111 °C
functional group   phosphine
SMILES string   CC12CC3(C)OC(C)(CC(C)(O1)P3c4ccccc4)O2
InChI   1S/C16H21O3P/c1-13-10-15(3)19-14(2,17-13)11-16(4,18-13)20(15)12-8-6-5-7-9-12/h5-9H,10-11H2,1-4H3
InChI key   AVVSJWUWBATQBX-UHFFFAOYSA-N

Description

Application

1,3,5,7-Tetramethyl-6-phenyl-2,4,8-trioxa-6-phosphaadamantane can be used:
• As a ligand to synthesize complexes for hydroformylation catalysis.
• To catalyze the synthesis of dibenzo[b,f][1,4]oxazepin-11(10H)-ones and 3-methyl-3,4-dihydrocoumarins by intramolecular cyclocarbonylation.

Packaging

2 g in glass bottle

500 mg in glass bottle

Safety & Documentation

Safety Information

RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 3
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable

Documents

Certificate of Analysis (COA)

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Protocols & Articles

Articles

Hydroformylation

Despite a long-standing belief that formyl groups cannot be generated at quaternary carbon centers via hydroformylation, Clarke and Roff have developed a method utilizing 1,3,5,7-tetramethyl-6-phenyl...
Josephine Nakhla
Aldrich ChemFiles 2009, 9.2, 9.
Keywords: Chemfiles, Hydroformylations, Hydrogenations, Ligands

Trialkylphosphine for Morita-Baylis Hillman Reactions

The use of amines and phosphines in nucleophilic catalysis is well precedented; however, arguably one of the severe limitations with respect to exploiting the more nucleophilic, yet less basic, phosp...
Keywords: Catalysis, Organocatalysis

Peer-Reviewed Papers
15

References

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